OFFICE OF

CHEMICAL SAFETY AND

POLLUTION PREVENTION

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON D.C., 20460

December 12, 2011

PC Code: 044312

DP Bar Code: D394848

MEMORANDUM

SUBJECT: Tier I Human Health Drinking Water Assessment of Dinotefuran and its 

Transformation Products of Concern (MNG, DN, UF and DN-2-OH + DN-3-OH) 

in Support of Proposed IR-4 New Uses (Onion, Bulb and Green; Berry and

Small Fruit; Tuberous and Corm Vegetables; Peach; and Watercress)

TO: Sidney Jackson, Risk Manager Reviewer

Barbara Madden, Team Leader

Risk Integration, Minor Use and Emergency Response Branch

Registration Division (7505P)

and Barry O’Keefe, Biologist

Paula Deschamp, Branch Chief

Registration Action Branch III

Health Effects Division (7509P)

FROM: Ronald Parker, Ph.D., Senior Environmental Engineer

Environmental Risk Branch III

Environmental Fate and Effects Division (7507P)

THROUGH: Dana Spatz, Chief

Environmental Risk Branch III

Environmental Fate and Effects Division (7507P)

Executive Summary

This memo summarizes the Environmental Fate and Effects Division’s (EFED) Tier I human 

health drinking water assessment of dinotefuran and its transformation products of concern 

(MNG, DN, UF and DN-2-OH + DN-3-OH) in support of the following proposed new IR-4 uses: 

Onion, Bulb and Green (Subgroups 3-07A and 3-07B); Berry and Small Fruit (Subgroups 13-

07F and 13-07H); Tuberous and Corm Vegetables (Subgroup 1C); Peach; and Watercress.

Resulting EDWCs for parent dinotefuran for the two terrestrial crop groups with the highest 

annual application amount are 33.4 μg/L for surface water acute risk, 5.5 μg/L for surface water 

chronic risk and 1.07 μg/L for groundwater. (Background information on the FIRST and 

SCIGROW models and output files for crop groups 1C and 13-07F are included in Appendix 1 at 

the end of this assessment). 
Below see also the qualitative assessment performed for watercress which is typically cultivated 

in shallow, flowing water. The Agency does not currently have a methodology for exposure 

assessment for crops cultivated in flowing water. The EFED tier 1 rice model has therefore been 

used as the basis of the exposure assessment and the results have been characterized to reflect 

differences between the conditions represented in the rice model and the actual methods of 

watercress cultivation. The three main differences are (1) simulation of application efficiency 

(fraction of amount applied which is intercepted by the crop), (2) simulation of degradation of 

the pesticide in water after application and (3) simulation of flow through and downstream from 

the area of cultivation. Consideration of these three differences from the rice model plus 

extensive runoff dilution from areas of the watershed which are not used for watercress 

cultivation would be expected to produce concentration values substantially less than those of 

other labeled crops.

All values are less than the previous EDWC values calculated by EFED for pome and stone 

fruits (D389034) (Table 1). Therefore, the pome and stone fruit EDWCs are still recommended 

for assessing dinotefuran residues in drinking water. The drinking water assessment was 

conducted for total dinotefuran residues including parent, MNG, DN, UF, DN-2-OH, DN-3-OH

as recommended by the OPP Health Effects Division. Total EDWCs for dinotefuran residues in 

surface source drinking water are not expected to exceed 91.31 μg/L for the 1 in 10 year daily 

peak concentration and 25.16 for the 1 in 10 year annual average concentration. In ground 

water, the EDWC for dinotefuran residues is not expected to exceed 3.5 μg/L. No surface and 

ground water monitoring data are available for dinotefuran.

Table 1. Estimated Drinking Water Concentrations for Dinotefuran Total Residues (Parent + 

Degradates) for Use on Tuberous and Corm Vegetables (Crop Subgroup 1C), Berry and Small 

Fruits (Crop Subgroup 13-07F), and on Pome and Stone Fruits 

Crop (Scenario) Percent 

Cropped 

Area 

(PCA)

Acute (peak) 

Surface Water 

Concentration 

(μg/L)

Annual Average 

Surface Water 

Concentration 

(μg/L)

Ground Water 

Concentration 

(μg/L)

Tuberous and Corm Vegetables

Crop Subgroup (1C); Berry and

Small Fruit Crop Subgroup (13-

07F). (1 aerial appl @ 0.338 lbs 

ai/A) Parent Only

100%1 33.4 5.5 1.07

Degradates

MNG 100%1

2.67 1.12 0.33

DN 100%1

5.38 2.28 0.07

UF 100%1

2.82 1.42 0.12

DN-2-OH2 100%1

8.23 4.09 0.37

Parent + All Degradates

Tuberous and Corm Vegetables

crop subgroup (1C); Berry and

Small Fruit crop subgroup (13-

07F). (Assuming All Peaks Occur 

Simultaneously)

100%1 52.51 14.42 1.97
Document 044312 D389034 Dinotefuran Section 18 Drinking Water , May 26, 2011

Parent + All Degradates

(Pome & Stone Fruits) (2 aerial 

appl @ 0.304 lbs ai/A) (Assuming 

All Peaks Occur Simultaneously)

100%1 91.31 25.16 3.5

1 http://www.epa.gov/oppefed1/models/water/pca_adjustment_dwa.html

2 DN-2-OH represents DN-2-OH+DN-3-OH. These two were reported as one metabolite in MRID 45640105.

Models Used and Modeling Inputs

The estimated drinking water concentrations for all terrestrial crops in this exposure assessment 

were estimated using the screening-level FQPA Index Reservoir Screening Tool (FIRST) model. 

The Tier 1 SCIGROW model was used to estimate concentrations in groundwater. Background 

information on the FIRST and SCIGROW models is included in Appendix 1, Page 15 of this 

report, at the end of this assessment.) For watercress, the only aquatic-based crop, the Tier 1 rice 

model was used. Watercress is grown in shallow, flowing water and cannot be simulated with the 

FIRST model. All model output files and a description of the EFED Tier 1 rice model are also 

included in Appendix 1.

Modeling inputs for parent dinotefuran are presented in Table 3. Modeling inputs and the 

calculation method used for the four degradates is included in the dinotefuran drinking water 

assessment for leafy brassica greens (See 044312 D357111 DWA Dinotefuran Leafy Brassica 

Greens, January 23, 2009 in Appendix 2 at the end of this report.). Under this method, each 

degradate is formed at the same ratio to the parent concentration in the previous assessments. 

The peak parent to peak degradate concentration ratios used in these assessments are included in Table 2.

Table 2. Dinotefuran peak parent to peak degradate concentration ratios

Degradate concentration values are therefore calculated based on the magnitude of the parent 

compound. All peak concentrations are conservatively assumed to occur simultaneously. See 

also a complete summary of physicochemical properties and environmental fate and transport 

data for parent dinotefuran and degradates in Tables 8-13.

Table 3. Summary of FIRST, SCIGROW and EFED Tier 1 Rice Model Input Values for 

Dinotefuran

Environmental Fate

Parameter

Value Justification Source

Water Solubility 39,830 mg/L Measured value MRID 45640112

Parent/Acute Parent/Annual Ave Parent/GrWater

Dinotefuran Ratio Ratio Ratio

MNG 0.080 0.204 0.313

DN 0.161 0.415 0.069

UF 0.084 0.259 0.116

DN-2-OH1 0.246 0.744 0.342
Table 3. Summary of FIRST, SCIGROW and EFED Tier 1 Rice Model Input Values for 

Dinotefuran

Environmental Fate

Parameter

Value Justification Source

Organic Carbon Partition 

Coefficient (Koc; mL/g)

30.1 (FIRST)

6 (SciGrow)

FIRST: Represents the mean of the 

following values: 42, 45, 42, 6, 22, 

23.3, 31.4, 33.6, 25.3 mL/g for the 

parent compound. 

SciGrow: represents the lowest value

MRID 45640114, 

45640115

Partition Coefficient (Kd; 

mL/g)

0.656 (Tier1 

Rice Model)

Mean Kd (from the following values: 

1.01, 0.71, 1.22, 0.12, 0.22 L/kg)

MRID 45640114

Aerobic Soil Metabolism Halflife (days)68 (FIRST)

38 (SciGrow)

FIRST: Represents the 90th percentile 

confidence bound on the mean halflife value of the following values: 

87.7, 38, 17, 78, 89, 20, 15.9 days

(four or more values)

SciGrow: Median value

MRID 45640111, 

45640112 / 46751101, 

46711201

Aerobic Aquatic Metabolism 

Half -life (days)

82.7 (FIRST) Represents the 90th percentile 

confidence bound on the mean halflife. Two available values: 79.3 and 

76.0 days; mean=77.65 days; standard 

dev.= 2.3335 days

MRID 45640117

Aqueous Photolysis Half-life 

(days)

1.8 (Rice) Single Available Value MRID 45640105

Characterization of Exposure Assessment for Watercress

The only aquatic crop in this assessment is watercress which is grown in clean, flowing water 2-

3 inches deep (see URLs: http://www.naturesherbal.com/Watercress.htm or 

http://edis.ifas.ufl.edu/mv151). The Agency does not currently have a methodology for exposure 

assessment for crops cultivated in flowing water. The EFED tier 1 rice model has therefore been 

used as the basis of the assessment and the results have been characterized to reflect differences 

between the capabilities of this model and the methods of cultivation of watercress. The three 

main differences are (1) simulation of application efficiency (fraction of amount applied which is 

intercepted by the crop), (2) simulation of degradation of the pesticide after application and (3) 

simulation of flow through the area of cultivation. A description of the EFED tier 1 rice model is 

included in Appendix 1.

Initial Simulation Using Tier 1 Rice Model

The Tier 1 rice model assumes dinotefuran application to watercress growing in a static rice 

paddy. The only process simulated by the model is partitioning of the applied chemical between 

the 10-centimeter deep water column and the 1-centimeter deep sediment layer of the paddy. The 

partitioning is based on the pesticide’s Kd. Resulting initial concentration in the rice paddy for 

parent dinotefuran for a single application of 0.36 pounds a.i., assuming an application efficiency 

of 0.0 (i.e. none of the pesticide remains on the watercress plants) is 355.4 μg/L. Under the 

conservative assumption that the peak concentrations of the parent and all degradates occur 
simultaneously, degradate concentrations for the three degradates formed by aqueous photolysis 

(DN plus UF plus DN-2-OH) would add a total of 49.2% of the parent concentration. This would 

yield an overall total of 530.3 μg/L. Degradation in the paddy is not calculated by the model so 

the pesticide is assumed to remain at this concentration in the water indefinitely. (These 

concentrations values by themselves do not represent EDWC values because watercress will not 

grow under the static water conditions represented in the rice model).

Impact of Simulating Application Efficiency

Under actual conditions of watercress cultivation, the major part of the applied pesticide will remain on 

the leaves of the watercress. This fraction is referred to as the application efficiency. The application 

efficiency goal of 1.0 is never achieved. The fraction on the leaves will also degrade and a portion of it 

may be washed off of the leaves by rainfall into the stream water below. Table 4 presents the impact of 

application efficiency on the initial concentration in the rice paddy water.

Table 4. Impact of Application Efficiency

Application Efficiency 

(fraction)

Initial Conc. in the Rice 

Paddy Water (μg/L)

0 530.0

0.1 477.0

0.2 424.0

0.3 371.0

0.4 318.0

0.5 265.0

0.6 212.0

0.7 159.0

0.8 106.0

0.9 53.0

1.0 0.0

Impact of Simulating Pesticide Degradation

Under field conditions, this concentration will be rapidly reduced through degradation by aerobic 

aquatic metabolism (half-life 82.7 days) and aquatic photolysis in the clear, shallow water (halflife: 1.8 days). Combined half-life is 1.76 days. Table 5 reflects 30 days of degradation at the 

combined degradation rate. This assumes an application efficiency of zero (0.0) and no flow.

Table 4. Reduction of Initial Dinotefuran Concentrations Parent + Aqueous Photolysis 

Degradates in Static Rice Paddy Water Due to Aqueous Photolysis

Days After Concentration Days After Concentration Days After Concentration

Application (μg/L) Application (μg/L) Application (μg/L)

0 530.300 11 6.968 22 0.092

1 357.669 12 4.699 23 0.062

2 241.236 13 3.170 24 0.042

3 162.706 14 2.138 25 0.028

4 109.739 15 1.442 26 0.019

5 74.016 16 0.972 27 0.013
6 49.921 17 0.656 28 0.009

7 33.670 18 0.442 29 0.006

8 22.709 19 0.298 30 0.004

9 15.317 20 0.201 31 0.003

10 10.331 21 0.136 32 0.002

Impact of Simulating Flow through the Cultivated Area

Under actual conditions of watercress cultivation, the amount of pesticide which reaches the stream water 

will be removed continuously downstream from the site at which it is applied by advection in the flowing 

water. The rate of removal depends on the rate of flow through the site. River velocity varies from day to 

day based on the volume of flow and changing cross-sectional area. Typical ranges of velocity vary from 

zero (at the time of tidal flow direction change) to 7 miles per hour (URL: 

http://hypertextbook.com/facts/2006/NervanaGaballa.shtml. The Mississippi River ranges from 1.2 to 3 

miles per hour depending on the amount flow and the reach in which it is measured. The pesticide in the 

flowing water will also spread from the center of mass during the flow. Table 6 presents the distance 

downstream of the center of mass of the applied dinotefuran.

Table 6. Downstream Movement from Site of Application of Dinotefuran in Flowing Water in One 

Day

Flow Rate

(ft/sec)

Flow Rate 

(mi/hour)

Downstream 

Distance (mi)

Flow Rate 

(ft/sec)

Flow Rate 

(mi/hour)

Downstream Distance

(mi)

0.1 0.1 3.5 1.6 2.3 56.3

0.2 0.3 7.0 1.7 2.5 59.8

0.3 0.4 10.6 1.8 2.6 63.4

0.4 0.6 14.1 1.9 2.8 66.9

0.5 0.7 17.6 2.0 2.9 70.4

0.6 0.9 21.1 2.1 3.1 73.9

0.7 1.0 24.6 2.2 3.2 77.4

0.8 1.2 28.2 2.3 3.4 81.0

0.9 1.3 31.7 2.4 3.5 84.5

1.0 1.5 35.2 2.5 3.7 88.0

1.1 1.6 38.7 2.6 3.8 91.5

1.2 1.8 42.2 2.7 4.0 95.0

1.3 1.9 45.8 2.8 4.1 98.6

1.4 2.1 49.3 2.9 4.3 102.1

1.5 2.2 52.8 3.0 4.4 105.6

The combination of application efficiency, pesticide degradation and stream flow in Tables 4, 5

and 6 plus runoff dilution from the areas in the watershed which are not treated are expected to

reduce the concentrations to a level substantially below that of the terrestrial crops modeled: i.e. 

soil half-life of 68 days and water half-life of 82.7 days). Degradation for five (5) days by itself 

will reduce the concentration to a level below the current drinking water exposure level (91.31

μg/L) given at the beginning of this report.
Application Amounts and Timing 

Labels indicate the timing of applications and use of the higher specified rates are triggered by severe 

pest pressure. For mealybug control, in the Berry and Small Fruit crop group only, the label calls for 

application between budbreak and peaberry size of the fruit.

Table 7. Proposed Application Rates for Dinotefuran in this New Use Drinking Water Assessment: 

IR-4 PR Numbers: 08645, 09832, 09550, 09548, 09514, 08596, 10727, 10728 ; Labels Dinotefuran 20SG, 

Dinotefuran 70 SG and Sparkle 70 SG

Crop Maximum 

application rate 

per application (lb 

a.i./A)

Maximum 

seasonal 

application rate 

(lb a.i./A)

Foliar (F) 

Soil (S)

Ground (G) 

and/or Aerial 

(A) allowed 

for foliar 

applications

Timing (T)

Berry and Small Fruit

(Subgroup 13-07F)

Small Fruit Vine Climbing, except Fuzzy 

Kiwifruit

Amur River Grape

Gooseberry

Grape

Kiwifruit, hardy

Maypop

Schisandra berry

Cultivars, Varieties

and/or hybrids of these

Foliar:

(0.045 to 0.135 lb 

ai/A) @ 14 days 

interval

Or

Soil:

(0.225 to 0.338 1b 

ai/A) @ 14 days 

interval

Foliar:

(0.270 lb ai/A) 

Soil:

( 0.338 lb ai/A)

F,S G,A

(T) For 

mealybug 

control, apply 

between 

budbreak and 

peaberry size.

Berry and Small Fruit

(Subgroup 13-07H)

Low Growing Berry Subgroup, except 

Strawberry

Bearberry

Bilberry

Blueberry Lowbush

Cloudberry

Cranberry

Lingonberry

Muntries

Partridgeberry

Cultivars, varieties and/or

hybrids of these

Foliar:

(0.090 to 0.180 lb 

ai/A) @ 14 days 

interval

Foliar

(0.360 lb a.i./A)

F G,A

(T) For 

mealybug 

control, apply 

between 

budbreak and 

peaberry size.

Tuberous and Corm Vegetables

(Subgroup 1C)

Arracacha

ArrowRoot

Artichoke, Chinese

Artichoke, Jerusalem

Canna, edible

Cassava, bitter and sweet

Chayote (root)

Chufa

Dasheen (taro)

Ginger

Leren

Potato

Sweet Potato

Tanier

Turmeric

Yam bean

Yam, true

Foliar: 

0.045 to 0.068 lb 

ai/A @ 14 days 

interval

Or 

Soil: 

0.293 to 0.338 lb 

ai/A

@ 14 days interval

Foliar

0.203 lb ai/A

Or 

Soil 

0.338 lb ai/A

F, S

Do not 

combine 

foliar app. 

with soil 

applications, 

or vice versa.

G, A

Onion, Bulb and Green

(Subgroups 3-07A and 3-07B)

Bulb onion, Includes:

Foliar: 

0.090 to 0.180 lb 

ai/A @ 7 days 

Foliar

0.270 lb ai/A

F, S

Do not 

combine 

G, A
Table 7. Proposed Application Rates for Dinotefuran in this New Use Drinking Water Assessment: 

IR-4 PR Numbers: 08645, 09832, 09550, 09548, 09514, 08596, 10727, 10728 ; Labels Dinotefuran 20SG, 

Dinotefuran 70 SG and Sparkle 70 SG

Crop Maximum 

application rate 

per application (lb 

a.i./A)

Maximum 

seasonal 

application rate 

(lb a.i./A)

Foliar (F) 

Soil (S)

Ground (G) 

and/or Aerial 

(A) allowed 

for foliar 

applications

Timing (T)

Daylily, bulb

Fritillaria, bulb

Garlic, bulb

Garlic, Great-headed, bulb

Garlic, serpent, bulb

Lily, bulb

Onion, bulb

Onion, Chinese, bulb

Onion, pearl

Onion, potato, bulb

Shallot, bulb

Cultivars, varieties and/or

hybrids of these

Green onion, includes:

Chive, fresh leaves

Chive, Chinese, fresh leaves

Elegans hosta

Fritillaria leaves

Kurrat

Leady's leek

Leek

Leek, wild

Onion, Beltsville bunching

Onion, fresh

Onion, green

Onion, macrostem

Onion, tree, tops

Onion, Welsh, tops

Shallot, fresh leaves

Cultivars, varieties and/or

hybrids of these

interval

Or 

Soil: 

0.225 to 0.270 lb 

ai/A

@ 7 days interval

Or 

Soil 

0.270 lb ai/A

foliar app. 

with soil 

applications, 

or vice versa.

Peach and Nectarine

Peach

Nectarine

Foliar: 

0.090 to 0.180 lb 

ai/A @ 7 days 

interval

Or 

Soil: 

0.225 to 0.270 lb 

ai/A

@ 7 days interval

Foliar:

0.270 lb ai/A

Or 

Soil:

0.270 lb ai/A

Overall per 

season:

0.360 lb ai/A

F, S G, A

Watercress Foliar:

(0.090 to 0.180 lb 

Foliar:

0.360 lb ai/A)

F G

3.3. Environmental Fate and Transport

Fate properties

Dinotefuran has a molecular weight of 202.2 g/mole, a very high water solubility (39,830 mg/L), 

and a low octanol/water partition coefficient (Kow = 0.283; log Kow = -0.549), suggesting a

potential for low bioaccumulation. The low vapor pressure (1.275 x 10-8 mm Hg) and a low 
Henry’s Law Constant (8.63 x 10-14

atm • M3/mol) suggest that this compound is not expected to 

volatilize substantially from water or soils in the environment. The physico-chemical properties 

of dinotefuran are listed in Table 8.

Table 8. Physicochemical Properties for Dinotefuran

Parameter Value Reference/ Comments

Selected Physical Chemical Parameters

Chemical Classification Nitroguanidine

Pesticide Classification Systemic Insecticide

Molecular Weight 202.2 g/mol MRID # 45640101

Water Solubility (20oC) 39,830 mg/L for parent

 

MRID# 45640112

Vapor pressure (30oC) <1.275x10-8 mm Hg 

(equivalent to <1.7 x 10-6 Pa)

MRID# 45640105

MRID# 45639702

Henry's Law Constant 8.63 x 10-14 Atm m3/mol Calculated

Octanol/Water Partition, Kow 0.283 @25oC MRID # 45639702

log KOW -0.549 MRID # 45639702

Dissociation constant (pKa) 12.6 @20oC (estimated) MRID # 45639702

Melting point 107.5oC MRID # 45639702

pH 5.6 @25oC MRID # 45654201

Density 1.40 g/cm3 @20oC MRID # 45639702

Solvent solubility (mg/L at 20°C) g/100 mL Solvent MRID # 45639702

Hexane 9 x 10-7

Heptane 1.05 x 10-6

Xylene 0.0072

Toluene 0.0149

Dichloromethane 6.45

Acetone 6.13

Methanol 6.00

Ethanol 2.01

Ethyl Acetate 0.52

UV/visible absorption spectrum Media Absorbance 

Maximum 

268 nm

€max: Molar

Absorbance 

Coefficient

MRID # 45639702

Acidic 1.0469 12,600

1.0180 12,300

Neutral 1.3017 12,500

1.2668 12,300

Basic 0.8869 10,700

0.9662 11,700

Environmental fate properties for dinotefuran are shown in Table 9. Potential routes of 

dissipation for dinotefuran are aqueous photolysis, leaching, and runoff. It is stable to abiotic 

hydrolysis, but rapidly photodegrades in water half-life 1.8 days. Major photodegradation 

products (>10% applied radioactivity) include 1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl) 

guanidine (UF), 1-methylguanidinium chloride (MG hydrogen chloride) , DN-2-OH + DN-3-

OH, 3-(Methylamino)-9-oxa-2-aza-4-azoniabicyclone-3-ene hydrogen succinate (BCDN 

succinate). DN is a minor photodegradation product (<10% applied radioactivity). Dinotefuran 

is moderately persistent in soil under both under aerobic (half-life = 16-100 days) and anaerobic 

(half-life = 62 days) conditions. Dinotefuran degrades to form 1-methyl-2-nitroguanidine 

(MNG), which subsequently degrades to form nitroguanidine (NG). It is very highly mobile 

(Koc = 6-45) in soil. Because dinotefuran has low sorption coefficients in soil, it has a high 

potential to leach and runoff from the application site. The fate of dinotefuran in aquatic 

environments will depend on the type of water body. Aqueous photolysis should be important in 

clear and shallow bodies of water; however, in deep ponds lakes or reservoirs, aquatic

metabolism is expected to dominate the dissipation processes. Dinotefuran was moderately 

persistent under actual use conditions in CA, NY, and GA field studies. The major degradation 
product was identified as MNG. Although there was no detection of dinotefuran in deep soil 

samples, MNG was detected in 15 to 30 cm soil layers in the GA field dissipation study. 

Table 9. Environmental Fate Properties for Dinotefuran

Parameter Value Reference/ Comments

Hydrolysis Half-life stable MRID# 45640102 (s)

MRID# 45640102 (a)

Photodegradation in Water Half-life 1.8 days MRID# 45640105 (s)

Photodegradation in Soil Half-life Stable MRID# 45640109 (u)

Aerobic Soil Metabolism Half-life 38 days , Loamy Sand Soil

17 days, Loam Soil

78 days, Loam soil

89 days, Loamy Sand soil

63 days, Loamy Sand soil

100 days, Loamy Sand soil

87.7 days, Loamy Sand soil 

15.9 days, Silt Loam soil

MRID# 45640111 (s)

MRID# 45640112(s) 

MRID#’s 46751101(a) 

MRID#45640112(a)

MRID# 46711201 (s)

Anaerobic Soil Metabolism Half-life 65 days MRID# 45891616 (s)

Aerobic Aquatic metabolism Half-life 79.3 days

76.0 days 

MRID # 45640117 (s)

Anaerobic Aquatic metabolism Half-life Entire system: 65.0 days 

Water: 51.0 days 

Soil: 62.0 days 

MRID# 45891616 (s)

Batch Equilibrium Texture Kd Koc

Loam 1.01 42

Sandy Loam 0.71 45

Clay Loam 1.22 42

Loamy Sand 0.12 6

Silt Loam 0.22 22

MRID# 45640114 (a)

Terrestrial Field Dissipation CA (SL) t1/2 = 65.2 days 

MNG (degradate) was detected in 0-

15 cm soil at 31.5% @ 45 days after 

2nd application.

GA (SL) t1/2 = 19.4 days 

MNG was detected in 0-15 cm soil at 

5.3% max. mean concentration after 

7 and 30 days after the 2nd

application.

NY (SL) t1/2 = 55.9 days 

MNG was detected in 0-15 cm soil at 

6.6% @ 45 and 120 days after the 

second application.

Applied 2X @ 0.268 lb a.i/A @ 14-

day interval to bare soil.

MRID# 45640118 (a)

Accumulation in Fish, max. BCF NA Waived (KOW = 0.28)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study (u)=unacceptable; NA=Not Available; 

N/A=Not Applicable

The degradation products of dinotefuran are shown in Table 10. MNG, is the major degradation 

product in soil. DN, UF, MG hydrogen chloride, DN-2-OH+DN-3-OH, and BCDN succinate 

are major degradation products in aquatic environments. These degradation products are formed 

through metabolism (i.e., DN) or photodegradation (i.e., DN, UF, MG hydrogen chloride, DN-2-

OH+DN-3-OH, and BCDN). 
MNG contains the nitro guanidine structure and therefore is considered to possess similar 

toxicity as the parent. DN is also structurally similar to the parent and therefore is considered to 

exhibit similar toxicity as the parent. Given the structures of the remaining degradates, they are 

expected to be less toxic than the parent (MARC memo USEPA 2004, D293759).

Table 10. Dinotefuran Degradates Identified in Environmental Fate Studies 

Short 

names

Structure Study Name

Results (calculated or observed halflife, degradates, and quantities, in 

% applied)

MNG

Aerobic Soil Metabolism

Maximum 23.96% at 42 days 

(preliminary study)

Maximum 13.7% at 225 days 

(conducted on radiolabeled parent), 

study termination

Terrestrial Field Dissipation

Maximum 31.5% at 45 days after 2nd

application; study termination at 170 

days after 2nd application

DN

Anaerobic Soil Metabolism

Maximum 29.2% at 120 days in 

Switzerland soil

Aerobic Aquatic Metabolism

Maximum 23.1% at 180 days in river 

system and 32.6% at 103 days in pond 

system

Photolysis in Water Maximum 7.5% at 11 days

UF Photolysis in Water Maximum 10.6% at 13.8 days (last 

test interval) 

MG 

hydrogen 

chloride

Photolysis in Water

Maximum 10.2% at 1.8 days, and 

0.8% at 13.8 days (final sampling 

interval)

DN-2-OH 

+ DN-3-

OH1

Photolysis in Water

Maximum 28.2% at 13.8 days (study 

termination)

BCDN 

Succinate Photolysis in Water

Maximum 16.1% at 1.8 days and 

4.5% at 13.8 days (study termination)

Environmental fate properties for MGN are shown in Table 11. Potential routes of dissipation 

include photodegradation, leaching, and runoff. MGN is stable to abiotic hydrolysis at pH 4, 7, 

and 9. It rapidly photodegrades (t1/2= 2.4 days) in water. MGN is moderately persistent (t1/2= 

66.9 to 166 days) in soil and persistent (t 1/2= 459 days) in aquatic environments. It has low 

soil:water portioning coefficients (Kd < 1; Koc <31), suggesting a potential for leaching and 

runoff. Field dissipation studies showed MGN residue detections in the 15-30 cm soil layer in a 

GA field study. These data suggest a leaching potential under actual use conditions. 

Table 11. Physicochemical and Environmental Fate Properties for Dinotefuran

Degradation Product-MGN 

Parameter Value Reference/ Comments

N

H

H2N

N

CH3

NO2

O N

H

NH

N

H

CH3

H3PO4

O N

H

O

N

H

CH3

NH

N

H

H2N

CH3

ClH

O

H

N NH

HN

OH

COOH

COOH

2

HN N

O

HN

CH3

COOH

COOH
Table 11. Physicochemical and Environmental Fate Properties for Dinotefuran

Degradation Product-MGN 

Parameter Value Reference/ Comments

Selected Physical Chemical Parameters

Water Solubility (20oC) 11,480 mg/L MRID# 45640112

MRID# 45639702, 45639706, 

45639707 (USEPA Pesticide 

Fact Sheet, 2004)

Hydrolysis Half-life

 pH 4-9 (50oC)

 

stable MRID# 45640103 (s)

Photodegradation in Water Half-life 2.4 days MRID# 45640107 (s)

Aerobic Soil metabolism Half-life 66.9 days in Silt Loam soil 

166 days in Sandy Loam soil

72.5 days in Clay Loam soil

MRID# 46711202 (s)

Aerobic Aquatic metabolism t1/2 459.3 days MRID # 45640117 (USEPA 

Pesticide Fact Sheet, 2004)

Mobility in Soils Texture Kd KOC

Loam 0.75 31

Sandy Loam 0.12 8

Clay Loam 0.70 24

Loamy Sand 0.16 8

Silt loam 0.16 16

MRID# 45640116 (s)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not 

Available; N/A=Not Applicable

Environmental fate properties for DN-phosphate1 are shown in Table 12. Potential routes of 

dissipation include photodegradation, microbial-mediated metabolism, leaching, and runoff. Nphosphate is stable to abiotic hydrolysis at pH 4, 7, and 9). Photodegradation is slow (t1/2= 53.4 

to stable days) in water at pH 5, 7, and 9. It is moderately persistent (t1/2= 114 days) in soil and 

aquatic environments. DN-phosphate has low soil:water portioning coefficients (Kd < 3; Koc 

58-413) in loam and sandy loam textured soils. Higher soil:water partitioning coefficients (Kd: 7 

- 72; Koc: 270-2502) were found in clay textured soils. These data suggest the extent leaching or 

runoff of DN-phosphate is dependent on soil properties such as texture and organic carbon 

content. 

Table 12. Physicochemical and Environmental Fate Properties for Dinotefuran

Degradation Product DN-Phosphate

Parameter Value Reference/ Comments

Selected Physical Chemical Parameters

 1 DN phosphate (1-methyl-3-(tetrahydro-3-furylmethyl)guanidinium dihydrogen phosphate) was identified as a 

degradation product of dinotefuran in photodegradation in soil (MRID 45640109), photodegradation in water 

(MRID 45640106, 45640105) and anaerobic soil metabolism (MRID 45891616) studies. Although the phosphorus 

is not an elemental constituent of parent dinotefuran, DN phosphate was formed as a salt of orthophosphate and 1-

methyl- 3-(tetrahydro-3-furylmethyl)guanidinium. Because the DN phosphate salt will dissociate in soil and aquatic 

environments to form (1-methyl-3-(tetrahydro-3-furylmethyl)guanidinium) and phosphoric acid, it is not expected to 

alter the environmental fate or toxicity of the organic moiety of DN phosphate (1-methyl-3-(tetrahydro-3-

furylmethyl)guanidinium). 
Table 12. Physicochemical and Environmental Fate Properties for Dinotefuran

Degradation Product DN-Phosphate

Parameter Value Reference/ Comments

Water Solubility (20oC) 619,400 mg/L MRID# 45640112

MRID# 45639702, 45639706, 

45639707 (USEPA Pesticide 

Fact Sheet, 2004)

Hydrolysis Half-life

DN-Phosphate pH 4-9 (50oC)

stable MRID# 45640104 (s)

Photodegradation in Water Half-life 

 pH 5

pH7

pH9

53.4 days 

Stable (533.2 days) 

Stable

MRID# 45640108 (s)

Aerobic Soil Metabolism Half-life

DN

114 days MRID# 45640117 (USEPA 

Pesticide Fact Sheet, 2004)

Aerobic Aquatic metabolism t1/2 114 days MRID# 45640117 (USEPA 

Pesticide Fact Sheet, 2004)

Mobility in Soils

DN-Phosphate

Texture Kd KOC

Loam 2.08 87

Sandy Loam 2.07 58

Clay Loam 72.54 2502

Sandy Loam 2.93 413

Clay 7.11 270

MRID# 45640113 (s)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not 

Available; N/A=Not Applicable

Environmental fate properties for UF are shown in Table 13. The potential route of dissipation 

is microbial-mediated metabolism. UF is stable to abiotic hydrolysis and photodegradation. It 

is moderately persistent in (t1/2= 60 days) in soil. 

Table 13. Physicochemical and Environmental Fate Properties for Dinotefuran

Degradation Product UF

Parameter Value Reference/ Comments

Selected Physical Chemical Parameters

Water Solubility (20oC) 4,171 mg/L for UF MRID# 45640112

MRID# 45639702, 45639706, 

45639707 (USEPA Pesticide 

Fact Sheet, 2004)

Hydrolysis Half-life

UF

Stable MRID# 45640102 (USEPA 

Pesticide Fact Sheet, 2004)

Photodegradation in Water Stable (~500 days) MRID# 45640105 (USEPA 

Pesticide Fact Sheet, 2004)

Aerobic Soil Metabolism Half-life 60 days (at mean) MRID# 45640111 (USEPA 

Pesticide Fact Sheet, 2004)

* (a) = acceptable study that fulfills guideline requirement; (s) = supplemental study; (u) = unacceptable study; NA=Not 

Available; N/A=Not Applicable

USEPA 2004. Dinotefuran. Report of the Metabolism Assessment Review Committee. Office of Prevention, 

Pesticides, and Toxic Substances. OPP/EFED. Washington, DC. January 20, 2004. TXR No. 0052304. DP Barcode 

D293759.
Figure 1. Dinotefuran and dinotefuran degradates (MTI-466)
Appendix 1.

Background information on FIRST and SCIGROW models and output files. 

Background Information on FIRST model:

FIRST (FQPA Index Reservoir Screening Tool) is a screening model designed to estimate the 

pesticide concentrations found in surface water for use in drinking water assessments. It 

provides high-end values on the concentrations that might be found in a small drinking water 

reservoir due to the use of pesticide. Like GENEEC, the model previously used for Tier I 

screening level, FIRST is a single-event model (one run-off event), but can account for spray 

drift from multiple applications. FIRST takes into consideration the so called Index Drinking 

Water Reservoir by representing a larger field and pond than the standard GENEEC scenario. 

The FIRST scenario includes a 427 acres field immediately adjacent to a 13 acres reservoir, 9 

feet deep, with continuous flow (two turnovers per year). The pond receives a spray drift event 

from each application plus one runoff event. The runoff event moves a maximum of 8% of the 

applied pesticide into the reservoir. This amount can be reduced due to degradation on field and 

the effect of binding to soil. Spray drift is equal to 6.4% of the applied concentration from the 

ground spray application and 16% for aerial applications.

FIRST also makes adjustments for the percent crop area. While FIRST assumes that the entire 

watershed would not be treated, the use of a PCA is still a screen because it represents the 

highest percentage of crop cover of any large watershed in the US, and it assumes that the entire 

crop is being treated. Various other conservative assumptions of FIRST include the use of a 

small drinking water reservoir surrounded by a runoff-prone watershed, the use of the maximum 

use rate, no buffer zone, and a single large rainfall.

FIRST Model

 RUN No.1 FOR Dinotefuran ON Crops Groups 1C & 13-07 * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .338( .338) 1 1 30.1 39830.0 AERIAL(16.0) 100.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 68.00 2 N/A 1.80- 223.20 82.70 60.34

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.1.0 JAN 1, 2007

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 33.384 5.487
 RUN No. 2 FOR Dinotefuran ON Turf Grass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .504( .504) 1 1 30.1 39830.0 AERIAL(16.0) 100.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 68.00 2 N/A 1.80- 223.20 82.70 60.34

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.1.0 JAN 1, 2007

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 49.780 8.181

 

Background Information on SCIGROW model:

SCIGROW (Screening Concentration in Ground Water) provides a groundwater screening 

exposure value to be used in determining the potential risk to human health from drinking water 

contaminated with the pesticide. Since the SCIGROW concentrations are likely to be 

approached in only a very small percentage of drinking water sources, i.e., highly vulnerable 

aquifers, it is not appropriate to use SCIGROW for national or regional exposure estimates.

SCIGROW estimates likely groundwater concentrations if the pesticide is used at the maximum 

allowable rate in areas where groundwater is exceptionally vulnerable to contamination. In most 

cases, a large majority of the use area will have groundwater that is less vulnerable to 

contamination than the areas used to derive the SCIGROW estimate.

Values below 0.006 ppb (6 ng/L) obtained by SCIGROW2.3 are beyond the scope of the 

regression data and have not been verified. If concerns are raised by exposures of less than 

0.006 ppb, a higher-tier ground water exposure assessment should be considered, regardless of 

how low a screening concentration is returned by SCIGROW. 

SCIGROW

 VERSION 2.3

 ENVIRONMENTAL FATE AND EFFECTS DIVISION

 OFFICE OF PESTICIDE PROGRAMS

 U.S. ENVIRONMENTAL PROTECTION AGENCY

 SCREENING MODEL

 FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:Dinotefuran

crop: pome and stone fruit

time is 5/20/2011 9: 9: 5

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)
------------------------------------------------------------------------

 0.304 2.0 0.608 6.00E+00 38.0

------------------------------------------------------------------------

groundwater screening cond (ppb) = 1.92E+00 

************************************************************************

SciGrow version 2.3

chemical:Dinotefuran

crop: pome & stone fruits

time is 5/23/2011 12:51:12

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.302 2.0 0.604 6.00E+00 38.0

------------------------------------------------------------------------

groundwater screening cond (ppb) = 1.91E+00 

************************************************************************

 

SCIGROW

 VERSION 2.3

 ENVIRONMENTAL FATE AND EFFECTS DIVISION

 OFFICE OF PESTICIDE PROGRAMS

 U.S. ENVIRONMENTAL PROTECTION AGENCY

 SCREENING MODEL

 FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:Dinotefuran

crop: Tuberous & Corm Vegetables time is 11/26/2011 11:06:08

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.338 1.0 0.338 6.00E+00 38.0

------------------------------------------------------------------------

groundwater screening cond (ppb) = 1.07E+00 

************************************************************************

EFED / OPP Tier I Rice Model

The EFED/OPP Tier I Rice Model version 1.0 relies on an equilibrium partitioning concept to 

provide conservative estimates of environmental concentrations resulting from application of 

pesticides to rice paddies. When a pesticide is applied to a rice paddy, the model assumes that it 

will instantaneously partition between a water phase and a sediment phase. The single, 

screening-level concentration calculated with this model represents both short and long term

surface water exposure and can be used for both aquatic ecological risk assessments and drinking 

water exposure assessments for human health risk assessment. The formula of the Tier I Rice 

Model v1.0 is as follows:

d

ai

w K

m C

0.00105 0.00013

'

+ =

and, if appropriate: 

Kd 01Koc = 0.

where:
Cw = water concentration [μg/L]

mai' = mass applied per unit area [kg/ha]

Kd = water-sediment partitioning coefficient [L/kg]

Koc = organic carbon partitioning coefficient [L/kg]

Note that neither the degradation of the pesticide nor the mass transfer from the aqueous phase to 

the sediment is considered in this conceptualization, which greatly simplifies the model. The 

absence of degradation adds conservatism to the model (i.e., estimated concentrations should be 

higher than those usually found in rice paddies). The absence of mass transfer processes can 

either add or reduce conservatism depending on numerous conditions such as whether the 

pesticide is soil or water applied and whether actual degradation occurs preferentially in the 

sediment or the water compartment; however, consideration of this parameter is a refinement 

beyond a Tier I conceptualization.

Physical Values of the Tier I Rice Model v1.0.

Parameter Symbol Value Reference

Water column depth dw 0.10 m USDA (1998, 2002)

Sediment depth dsed 0.01 m Calibration described in Section III C of this 

document.

Organic content of 

sediment

foc 0.01 Justification provided in Section III B of this 

document.

Sediment bulk density ρb 1300 

kg/m3

Brady (1984), Hillel (1982)

Grain density ρg 2650 

kg/m3

Density of quartz, typical assumption; 

Brady(1984), Hillel (1982)

Sediment porosity θsed 0.509 θsed = 1- (ρb/ρg)

Most of the assumptions used in this model help ensure that the outputs are protective of most 

environments associated with rice agriculture. The model assumptions include the following:

1. Movement of pesticide on suspended sediment is not considered.

2. Degradation does not occur.

3. Volatilization and other dissipation processes are not considered.

4. Partitioning to sediment is instantaneous.

5. Water is available for human or wildlife exposure instantaneously.

6. Water column depth is 10 cm.

7. Sediment depth is 1 cm.

8. All pore space is saturated with water.

9. Organic carbon fraction is 0.01.

10. Bulk density is 1300 kg/m3.

11. Grain density is 2650 kg/m3.
Appendix 2.

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON D.C., 20460

 OFFICE OF 

 PREVENTION, PESTICIDES AND

 TOXIC SUBSTANCES

January 23, 2009

PC Code: 044312

DP Bar Code: D357111

MEMORANDUM

SUBJECT: Tier I Estimated Drinking Water Concentrations of Dinotefuran and its 

Transformation Products of Concern MNG, DN, UF and DN-2-OH + DN-3-OH, 

for Use in Human Health Risk Assessment, Proposed New (IR-4) Use of the 

Chemical on Leafy Brassica Greens and Turnip Greens

TO: Sidney Jackson, Risk Manager Reviewer

Daniel Rosenblatt, Chief

Risk Integration, Minor Use and Emergency Response Branch

Registration Division (7505P)

and Barry O’Keefe, Biologist

Paula Deschamp, Branch Chief

Registration Action Branch III

Health Effects Division (7509P)

FROM: José Luis Meléndez, Chemist

Environmental Risk Branch V

Environmental Fate and Effects Division (7507P)

THROUGH: Mah Shamim, Ph.D., Chief

Environmental Risk Branch V
Environmental Fate and Effects Division (7507P)

The purpose of this memorandum is to provide the Estimated Drinking Waters Concentrations 

(EDWCs) of dinotefuran, an active ingredient of products such as SafariTM 20SG Insecticide and 

DINOTEFURAN 20SG Insecticide, and its transformation products MNG, DN, UF, and DN-2-

OH + DN-3-OH (for nomenclature and structures of these compounds, please, refer to Appendix 

B), due to the use of the chemical on various crops, turf and ornamentals, using soil, ground or 

aerial applications. EFED has reviewed the IR-4 petition, and found that the use with the highest 

rate per application and per season is still turf. Therefore, the EFED will rely on its January 21, 

2004 Tier I Drinking Water Analysis, with electronic copy attached to this document (Appendix 

C). Please, find below the Executive Summary and a table indicating the proposed EDWCs to be 

used. Should additional refinements are required by HED, please, contact us, so that the EFED 

may schedule tier 2 surface waters PRZM/EXAMS modeling. Should any questions arise, 

please, contact us.

EXECUTIVE SUMMARY 

Table 1 provides a summary of the Tier I modeled drinking waters concentrations. Please, refer 

to Appendix C for original memorandum.

Table 1. Tier I Estimated Drinking Water Concentrations

Chemical

Acute (peak) Surface 

Water Concentration (ppb)

Annual Average Surface 

Water Concentration (ppb)

Ground Water 

Concentration (ppb)

Dinotefuran 48.20 8.00 2.75

MNG 3.86 1.63 0.86

DN 7.77 3.32 0.19

UF 4.07 2.07 0.32

DN-2-OH1 11.88 5.95 0.94

1 - DN-2-OH represents DN-2-OH+DN-3-OH. These two were reported jointly in the study.

Dinotefuran, [CAS name N-methyl-N′-nitro-N′′-[(tetrahydro-3-furanyl)methyl]guanidine; IUPAC 

name (EZ)-(RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine], is a nitroguanidine 

insecticide. Its PC code is 044312 and its CAS number is 165252-70-0. Dinotefuran belongs to 

a broad group of insecticides commonly known as nicotinoid insecticides. Within the nicotinoid 

insecticides, dinotefuran belongs to the narrower class of insecticides known as nitroguanidine 

(also includes clothianidin, imidacloprid and thiamethoxan), they are nicotinic acetylcholine 

receptor agonists/ antagonists, group 4A insecticides (www.irac-online.org). These compounds 

target the nicotinic acetylcholine receptors (nAChR) site and activate post-synaptic acetylcholine 

receptors. Dinotefuran, like other neonicotinoids, acts as an agonist of acetylcholine, the 

neurotransmitter that stimulates the nAChR. Acetylcholine (ACh) is the endogenous agonist and 

excitatory neurotransmitter of the cholinergic nervous system. Neurotransmission through the 

nicotinic cholinergic synapse is mediated in two steps. First, ACh is released from the 

presynaptic membrane by exocytosis and interacts with the binding site located at the 

extracellular domain of the nAChR/ion channel complex. Second, a formational change of the 

receptor molecule leads to opening the ion channel, promoting the influx of extracellular Na+ and 

efflux on intracellular K+ to disrupt the equilibrium status of the membrane potential. (Please, 

refer also to original S3 New Chemical review dated June 30, 2004.)
Currently, dinotefuran is used in various crops such as cotton, head and stem brassica (broccoli, 

cabbage, cauliflower), cucurbits (watermelon, cucumber), fruiting vegetables (pepper, tomato), 

grapes, leafy vegetables (lettuce) and potato; it is used also on ornamental plants and turf. 

However, the maximum application rate is on turf.

This action is an Interregional Project No. 4, for the proposed use of dinotefuran on leafy 

brassica greens (Subgroup 5B), including turnip greens (broccoli raab, Chinese cabbage (Bok 

Choy), collards, kale, mizuna, mustard greens, mustard spinach, rape greens and turnip greens). 

Please, refer to Appendix A for a summary of the use information gathered from the current and 

proposed labels.

This is a Tier I screening-level Drinking Waters Assessment (DWA). For surface waters the tier 

1 aquatic model FIRST was used, and for ground waters, the tier 1 aquatic model SCI-GROW 

was utilized. For the assessment, maximum application rates and minimum intervals between 

applications were used (note: for turf a single application was assumed). The Metabolism 

Assessment Review Committee’s (MARC) decision document concluded that the transformation 

products MNG, DN, UF, and DN-2-OH + DN-3-OH of dinotefuran are of potential concern for 

drinking water sources. Therefore, EDWCs of these compounds were also simulated using 

FIRST and SCI-GROW models as explained in the memorandum attached. The approach used 

to calculate the transformation products was the individual degradate calculation, as opposed to 

the total residues calculations. 

The major data gaps are related to the transformation products MNG, DN, UF, and DN-2-OH + 

DN-3-OH; modeling was used to obtain some of the parameters needed for the estimation of the 

drinking water concentrations of the above mentioned degradates, using EPIWIN.
Appendix A. Current and Proposed Application Rates for Dinotefuran

Table A1. Current and Proposed Application Rates for Dinotefuran (data obtained from current and 

proposed labels for DINOTEFURAN 20SG, EPA Reg. No. 33657-17, STARKLE 70SG, EPA Reg. No. 33657-

38, DINOTEFURAN 70SG, EPA Reg. No. 59639-135 and DINOTEFURAN 20%, EPA Reg. No. 33657-16). 

New use appears shaded yellow and bolded.

Crop Maximum application 

rate per application 

(lb a.i./A)

Maximum 

seasonal 

application rate 

(lb a.i./A)

Foliar or Soil 

application 

allowed?

Ground or Aerial 

allowed for foliar 

applications?

Leafy Brassica Greens: Broccoli 

Raab, Chinese Cabbage (Bok Choy), 

Collards, Kale, Mizuna, Mustard 

Greens, Mustard Spinach, Rape 

Greens, Turnip Greens

0.141 @ 7 days 

interval

0.268 F

No more than 3 

applications 

per season are 

allowed.

G, A

Cotton 0.134 @ 7 days interval 0.268 F G, A

Head and Stem Brassica: Broccoli, 

Brussels sprouts, Cabbage, 

Cauliflower, Cavalo Broccolo, Chinese 

broccoli, Chinese cabbage, Chinese 

mustard cabbage, Kohlrabi

Foliar: 0.179 @ 7 days 

interval

Or

Soil: 0.33

0.268 Foliar

Or 

0.536 Soil

F, S

Do not combine 

foliar app. with 

soil applications, 

or vice versa.

G, A

Cucurbits: Balsam pear (bitter melon), 

Calabaza, Chayote (fruit), Chinese 

okra, Chinese waxgourd, Citron melon, 

Cucumber, Gherkin, Gourds, Edible 

melons including hybrids (including 

cantaloupe, casaba, Chinese preserving 

melon, Crenshaw, honeydew melons, 

honey balls, mango melon, 

muskmelon, Persian melon, winter 

melon), Pumpkin, Squash (including 

summer, winter acorn, spaghetti), 

Watermelon including hybrids

Foliar: 0.179 @ 7 days 

interval

Or

Soil: 0.33

0.268 Foliar

Or 

0.536 Soil

F, S

Do not combine 

foliar app. with 

soil applications, 

or vice versa.

G, A

Fruiting Vegetables: Eggplant, Ground 

Cherry, Pepinos, Pepper (including bell 

peppers, chili peppers, cooking 

peppers, pimentos and sweet peppers), 

Tomatillo, Tomato (do not apply to 

varieties of tomatoes which are less 

than 2 inches in size, such as cherry 

and grape tomatoes)

Foliar: 0.179 @ 7 days 

interval

Or 

Soil: 0.33

0.268 Foliar

Or 

0.536 Soil

F, S

Do not combine 

foliar app. with 

soil applications, 

or vice versa.

G, A

Grapes Foliar: 0.132 @ 14 

days interval

Soil: 0.33

0.264 Foliar

0.33 Ground

0.528 overall 

per season

F, S

Make only one 

soil application.

G w. airblast, A

Leafy Vegetables (Except Brassica 

Vegetables): includes: Amaranth, 

Arugula, Cardoon, Celery, Chinese 

Celery, Celtuce, chervil, Edible-leaved 

& Garland Chrysanthemum, Corn 

Salad, Garden & Upland Cress, 

Dandelion, Dock, Endive, Florence 

Fennel, Head & Leaf Lettuce, Orach, 

Parsley, Garden & Winter Purslane, 

Radichio, Rhubarb, Spinach, New 

Zealand & Vine Spinach, Swiss Chard

Foliar: 0.134 @ 7 days 

interval

Or 

Soil: 0.33

0.268 Foliar

Or 

0.536 Soil

F, S

Do not combine 

foliar app. with 

soil applications, 

or vice versa.

G, A

Potato Foliar: 0.066 @ 14 

days interval

0.198 Foliar F, S

Do not combine 

foliar app. with 

G w. airblast, A
Table A1. Current and Proposed Application Rates for Dinotefuran (data obtained from current and 

proposed labels for DINOTEFURAN 20SG, EPA Reg. No. 33657-17, STARKLE 70SG, EPA Reg. No. 33657-

38, DINOTEFURAN 70SG, EPA Reg. No. 59639-135 and DINOTEFURAN 20%, EPA Reg. No. 33657-16). 

New use appears shaded yellow and bolded.

Crop Maximum application 

rate per application 

(lb a.i./A)

Maximum 

seasonal 

application rate 

(lb a.i./A)

Foliar or Soil 

application 

allowed?

Ground or Aerial 

allowed for foliar 

applications?

Or 

Soil: 0.33

Or 

0.33 Soil

soil applications, 

or vice versa.

Turfgrass (commercial, residential, 

recreational)

Foliar

0.54

0.54 F G

Vegetable Transplants grown in 

enclosed structures, including 

Cucurbits, Fruiting Vegetables, Head 

and Stem Brassica and Leafy 

Vegetables (excluding Brassica spp.)

Foliar

0.18

0.268 F or Broadcast 

spray

G

Ornamental plants in greenhouses,

nurseries, interior plantscapes, lath and 

shadehouses and outdoor landscapes 

(commercial, industrial, recreational 

and residential) or Ornamental 

containerized or in ground plants

(including Shrubs, Bedding Plants, 

Flowering Plants, Foliage Plants, 

Ground Covers, Evergreens, 

Ornamental Plants and Trees, NonBearing Fruit Trees, Non-Bearing Nut 

Trees and Non-Bearing Vines)

Foliar

0.2

Soil

12-24 oz per gallon

0.54

0.54

F w. airblast (for 

trees and vines) 

or Broadcast 

spray, S

Do not make 

more than one 

soil application 

per crop cycle or 

three months, 

whichever is 

shorter.

G
Appendix B. Nomenclature and Structures of Dinotefuran and its Transformation 

Products

 Table B1. Nomenclature of Dinotefuran and its Transformation Products

Applicant's Code IUPAC Chemical CAS Name CAS No. PC 

Code

Dinotefuran/MTI-446 (RS)-1-methyl-2-nitro-3-(tetrahydro-3-furylmethyl) 

guanidine

N-methyl-N’-nitro-N”-

[(tertrahydro-3-furanyl)

methyl]guanidine.

165252-70-0 044312

DN-Phosphate 1-Methyl-3-(tetrahydro-3-furylmethyl) guanidinium 

dihydrogen phosphate

- - -

MNG 1-Methyl-2-nitroguanidine N-methyl-N’-nitro-guanidine 4245-76-5 -

UF 1-methyl-3-(tetrahydro-3-furylmethyl)urea - - -

DN-2-OH + DN-3-OH Bis[1-(3-hydroxytetrahydro-3-furylmethyl)-3-

methylguanidinium] terephthalate (DN-3-OH)

- - -

Dinotefuran [MTI-446] – Parent Compound

IUPAC Name: (EZ)-(RS)-1-Methyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine.

CAS Name: N-Methyl-N′-nitro-N′′-[(tetrahydro-3-furanyl)methyl]guanidine.

CAS Number: 165252-70-0.

SMILES String: CNC(=NN(=O)=O)NCC1COCC1 (ISIS v2.3/Universal SMILES).

No EPI Suite, v3.12 SMILES String found as of 9/29/06.

Unlabeled

O C

H2

N

H

C

N

N

H

NO2

CH3
1-Methyl-2-nitroguanidine [N-Methyl-N’-nitro-guanidine; MNG]

IUPAC Name: 1-Methyl-2-nitroguanidine.

CAS Name: N-methyl-N’-nitro-guanidine.

CAS Number: 4245-76-5.

SMILES String: NC(=NN(=O)=O)NC (ISIS v2.3/Universal SMILES).

N(=O)(=O)NC(=N)NC EPI Suite, v3.12 SMILES String found as of 

07/02/08.

1-Methyl-3-(tetrahydro-3-furylmethyl)urea [UF]

IUPAC Name: 1-Methyl-3-(tetrahydro-3-furylmethyl)urea.

CAS Name: Not reported.

CAS Number: Not reported.

N

H

H2N

N

CH3

NO2

O N

H

O

N

H

CH3
1-Methyl-3-(tetrahydro-3-furylmethyl)guanidinium dihydrogen 

phosphate [DN phosphate] (a salt of DN)

IUPAC Name: Not reported.

CAS Name: Not reported.

CAS Number: Not reported.

Bis[1-(3-hydroxytetrahydro-3-furylmethyl)-3-methylguanidinium] 

terephthalate

DN-3-OH

IUPAC Name: Bis[1-(3-hydroxytetrahydro-3-furylmethyl)-3-methylguanidinium] 

terephthalate.

CAS Name: Not reported.

CAS Number: Not reported.

O N

H

NH

N

H

CH3

H3PO4
O

HN NH

HN

OH

COOH

COOH

2
Appendix C. UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

 OFFICE OF

PREVENTION, PESTICIDES AND

 TOXIC SUBSTANCES

January 21, 2004

MEMORANDUM

PC Code: 044312

DP Bar Code: D290192

SUBJECT: Tier I Estimated Drinking Water Concentrations of Dinotefuran (MTI-446) and 

its major transformation products for use in Human Health Risk Assessment

TO: Meredith Laws, Branch Chief

Rita Kumar, PM Team Reviewer

Insecticide-Rodenticide Branch

Registration Division (7505C)

and Kathy Raffael, Risk Assessor

Health Effects Division (7509C)

FROM: Subijoy Dutta, P.E., Environmental Engineer

Environmental Risk Branch V

Environmental Fate and Effects Division (7507C)

THROUGH: Mah Shamim, Ph.D., Chief

Environmental Risk Branch V

Environmental Fate and Effects Division (7507C)

This memo presents the Tier I Estimated Drinking Water Concentrations (EDWCs) for 

dinotefuran (MTI-446), and for its major transformation products - MNG, DN, UF, and DN-2-

OH +DN-3-OH. These estimates are based upon calculations using FIRST (surface water) and 

SCIGROW (ground water) for use in the human health risk assessment. The Mitsui Chemical, 

Inc. is seeking registration for the new uses of the chemical on Leafy Vegetables, Turf Grasses, 

and Residential uses such as fly bait, ant bait, and house and garden ready to use spray. 
Page 29

Table 1. Tier I Estimated Drinking Water Concentrations

Chemical Acute (peak) Surface 

Water Concentration (ppb)

Annual Average Surface 

Water Concentration (ppb)

Ground Water Concentration 

(ppb)

Dinotefuran

(MTI-446)

48.20 8.00 2.75

MNG 3.86 1.63 0.86

DN 7.77 3.32 0.19

UF 4.07 2.07 0.32

DN-2-OH1 11.88 5.95 0.94

1 - DN-2-OH represents DN-2-OH+DN-3-OH. These were reported jointly as one metabolite in MRID 45640105.

The above values (Table 1) generally represent upper-bound estimates of the concentrations that 

might be found in surface water and groundwater due to the use of dinotefuran on Turfgrass, 

which represents the maximum application rate and worst case scenario. Both the surface and 

ground water models provide screening level estimates. Most of the physical properties of UF, 

and DN-2-OH were estimated by using the EPI win program. For lack of pertinent data, the 

biodegradation half life was also estimated by using the Biowin program for UF and DN-2-OH. 

It should be noted that the models used for the estimation of drinking water concentrations 

assumed the formation of UF and DN-2-OH. These degradates are photolysates and it appears 

that they are less likely to be formed in the ground spray scenario for turfgrass. Most of the 

formation of these degradates would be caused by direct exposure of surface waters to the parent 

by spray drift, followed by photolysis. EFED emphasizes that this is only a screening level 

analyses (Tier 1), and should there be a need by HED, additional refinements can be made if the 

registrant provides further studies addressing the degradate characteristics which should yield 

accurate input values for the models. 

Background Information About Dinotefuran, and Use on Leafy Vegetables, Turf grasses, 

and Residential use:

Dinotefuran is a selective systemic insecticide which is also known as MTI-446. The registrant, 

Mitsui Chemicals America, Inc. is presently proposing uses on leafy vegetables, turf grasses and 

various residential uses such as ant bait, fly bait, house and garden ready-to-use-spray, total 

release fogger, cat spot-on, 20% PCOs for pet sleeping areas, and Shuriken cockroach gel bait.

The principal mode of action of dinotefuran relates to its neonicotinoid and nitroiguadine 

subclass. From the label information it is evident that dinotefuran is toxic to bees exposed to 

direct treatment or to residue on blooming crops and weeds. Also, following an in-furrow or soil 

application of dinotefuran, no foliar application of dinotefuran or any other insecticide in the 

neonecotinoid class should be made. According to the label Dinotefuran may however be used 

in alternation with other materials possessing dissimilar modes of action and/or with other 

chemical classes of insecticides.
Page 30

Applications of dinotefuran in outdoors are expected to be by ground application (soil 

application or spray) or aerial spray methods. The application rate would vary according to the 

type of crop and disease; for leafy vegetables, granular soil incorporation a one-time application 

of 2.68 lbs of dinotefuran 20SG, i.e a maximum of 0.536 lb a.i/acre is allowed. For foliar sprays 

up to two applications are allowed with a limitation of a maximum 1.34 lbs of dinotefuran 20SG, 

i.e a total maximum of 0.268 lb a.i/acre per season for leafy vegetables. Table 2 provides the 

proposed use profile for dinotefuran.

Table 2. Dinotefuran Use Profile

Crop lbs ai/A/ 

Application

Max # 

applications

minimum 

application 

interval (days)

comments

Leafy Vegetable

Foliar

0.045-0.134

Soil

0.226-0.268

2 7

Regardless of the application method 

do not apply more than a total of 2.68 

lbs of Dinotefuran 20SG (0.536 lb a.i).

Turf Grasses

0.54 1 -

0.54 lb a.i/ac translates to 1.8 oz/1000 

square ft of Dinotefuran 10SL product

Approach for Dinotefuran

According to the label for dinotefuran the worst case scenario for use in the water assessment 

model is for use on Turf grasses. The maximum application rate provided in the label for this 

crop is the highest possible dosage of this chemical in a single application. Because of the high 

solubility of dinotefuran, the maximum potential for this chemical for migration through surface 

water runoff or leaching exist in this particular scenario amongst all of the different application 

rates and methodologies specified in the proposed labels provided by the registrant. The default 

percent cropped area (PCA) of 0.87 is used for Turf grasses. The EFED review of crop 

production data yielded approximate potential acreages for vegetables as 1,895,620 Acres (2001 

Census of Agriculture). 

Tables 3 summarizes the input values used in the model runs for FIRST1.0 and SCIGROW2.3, 

respectively. The lowest non-sand Koc was used in FIRST. The median Koc value was used in 

SCIGROW. There were two available aerobic soil metabolism half-lives for dinotefuran, 

obtained in one soil type in a radiolabeled study. The upper confidence bound value (90th

percentile) of the half-life was used for the aerobic soil metabolism in FIRST. The mean halflife was used in SCIGROW modeling. The modeling results associated with maximum 

allowable rate per year (0.536 lb ai/acre applied one time) are presented in Table 1. Copies of 

the orginal printouts from the modeling runs (FIRST and SCIGROW) are attached at the end of 

this memorandum.
Page 31

Approach for Dinotefuran’s Major Transformation Product

The Metabolism Assessment Review Committee (MARC) recommended Dinotefuran, DN, DN2-OH+DN-3-OH, MNG, and UF, as residues of concern for water in their minutes of the 

meeting held on January 7, 2004. Important transformation products of dinotefuran appear to be 

MNG and DN. However, one aqueous photolysis study had identified UF, DN-2-OH+DN-3-

OH, MG hydrogen chloride, and BCDN succinate as major transformation products. Since 

BCDN succinate and MG Hydrogen chloride were found to degrade further fairly quickly, there 

were no concern for these two degradates by the MARC. Out of these degradates MNG appears 

to be persistent and relatively mobile. Of these, MNG is more mobile and relatively persistent, 

but there is insufficient field data to confirm the laboratory findings. From the studies submitted 

by the registrant, the physical properties of only two transformation products, MNG and DN 

were only available partially for running the models. Only partial degradation characteristics 

was available for MNG from one study. No degradation characteristics were available for any 

other degradates from the studies submitted by the registrant.

Due to its high persistence, dinotefuran may be available for runoff or leaching. MNG, the 

transformation product, also appears to be persistent and relatively mobile. It is not expected to 

be available for runoff and leaching in highly detectable quantities because the laboratory studies 

indicated that it was present at a maximum of only 13.7% of the applied which is close to the 

limit of concern (10% of the applied). 

One mobility study was conducted on DN-phosphate, a salt of the degradate DN. DN-phosphate 

was found to be relatively less mobile compared to its parent as evidenced by its Koc values, 

which ranged from 58 to 2502 and yielded a mean Koc of 666. DN-phosphate is stable to 

hydrolysis and aqueous photolysis (~533 days at pH7).

From all of the fate studies submitted by the registrant, the aerobic soil metabolism half-life 

could be calculated for only one of the major degradate, MNG. Based upon the available 

information and data provided by the registrant, the degradate MNG was also simulated using 

the screening models, FIRST and SCIGROW. EFED had only limited environmental fate data 

for these transformation products; however, mobility data, a very important parameter in the 

screening models, was available for MNG and DN-phosphate as listed in Tables 3a and 3b at the 

end. Only one study (aerobic soil metabolism) submitted by the registrant had the minimum 

decline information for MNG to calculate its half-life. Based upon the detection of MNG in 

Findak Garden loam soil the estimated half-life for MNG in this soil was determined as 153 

days. Because of the availability of only one half-life value the input value was taken as 459 days 

(3x153) per the modeling guideline. This value was used in FIRST, and the single value was 

used for SCIGROW. MNG reached a maximum of 13.7% of the applied in the radiolabeled 

aerobic soil metabolism study. It is simulated by multiplying the label application rate by 0.137 

or 13.7% and then multiplying that by the mole ratio, i.e. molecular weight of MNG divided by 

the molecular weight of the parent (118/202.2) to yield 0.043 lb a.i/ac (0.54x0.137x118/202.2).

The mobility and solubility values for the degradate DN were provided in the studies submitted 

by the registrant for DN-Phosphate, a stable salt of DN. Although these studies provided a few 
Page 32

input parameters, but no aerobic soil metabolism half-life was provided for DN and hence it was 

assumed to be stable for running the FIRST model. One aerobic aquatic half-life was available 

from a study and was used as the input value for running the models. For the groundwater 

estimation by SCIGROW the aerobic aquatic half life was used since the degradate was formed 

only under aquatic condition. The aqueous photolysis half life was available for DN.

No data were available for the degradates, UF, and DN-2-OH+DN-3-OH (represented by DN-2-

OH) in any of the studies submitted by the registrant. The EPI Win program was run to estimate 

the mobility and solubility of these two degradates. The aerobic soil metabolism half lives were 

not available for DN, UF and DN-2-OH and also no aqueous photolysis half lives were not 

available for UF and DN-2-OH. The Biowin program was used to estimate the biodegradation 

half lives for UF and DN-2-OH. Since the structure of DN was very similar to DN-2-OH the 

aqueous photolysis half lives of these two degradates were assumed to be the same for the 

screening level model runs. For UF the aerobic soil metabolism was estimated by the Biowin 

program and the aqueous photolysis half life was assumed to be stable (i.e ~500 days). For 

screening level modeling runs these assumptions should provide only an upper-bound estimated 

concentration of the degradates in water. Should there be a need by HED, additional refinements 

can be made using a higher tier model. However, this will require further submission of studies 

by the registrant characterizing all of these degradates so that accurate input values for the 

models could be determined. 

The input parameters for Dinotefuran, MNG, DN, DN-2-OH, and UF are presented in Table 3a, 

3b, and 3c respectively. The modeling results are shown in Table 1. 
Page 33

Table 3a Environmental Fate and Other Input Parameters for Dinotefuran used in FIRST and SCIGROW

Parameter Dinotefuran MNG Source

Water Solubility (25°C) 39,830 ppm 11,480 ppm MRID #45640112

MRID#45639706

Hydrolysis Half-Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half-Life (upper 

confidence bound value, 90th percentile, 

from 2 values)

116.4 days 459.3

(3x one value)

MRID#45640112

MRID#45640111

Aerobic Soil Metabolism Half Calculated value(MNG) -Life (mean) 81.5 days 153.1 (1)

Aerobic Aquatic Metabolism Half-life

(upper confidence bound value, 90th

percentile, from 2 values)

80.8 days Calculated

2x459.3

= 918.6

MRID#45640117

Aqueous Photolysis Half-Life 1.8 days 2.4 days MRID#45640105

MRID#45640107

Adsorption/Desorption Coefficient (Lowest 

non-sand Kd)

0.22 0.16 MRID#45640114

MRID#45640116

Organic Carbon Adsorption/Desorption 

Coefficient (lowest non-sand KOC)

22 16

Pesticide is Wetted-In Yes Proposed Label

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other 

crops

Application Method(for Turfgrass 

application - max. Application rate)

Ground Spray(3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) 0.54 0.043 (4) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Half life for MNG was determined based upon the detection of two degrading concentrations of MNG in the aerobic soil 

metabolism study on Dinotefuran (MRID# 45640111)

(2). Mean value was selected for SCIGROW because two values were identical.

(3). Maximum application rate selected for Turfgrass, ground spray.

(4). Maximum concentration observed in the aerobic soil metabolism study x application rate x mole ratio = 

 (0.137)(0.54)(118/202.2)=0.043
Page 34

Table 3b Environmental Fate and Other Input Parameters for DN and DN-2-OH used in FIRST and 

SCIGROW

Parameter DN-2-OH DN Source

Water Solubility (25°C) 1000,000 ppm 

(1)

619,400 ppm EPI Win program

MRID#45639707

Hydrolysis Half-Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half-Life (3 times 

single value calculated by Biowin Program)

180 N/A Calculated half Life of 

DN-2-OH using Biowin 

program.

Assumed 114 days half 

life (DN) 

MRID#45640117.

Aerobic Soil Metabolism Half-Life (mean) 60 days 114 days (2)

Aerobic Aquatic Metabolism Half-life

(one value only)

342 days (N/A -

(assumed same 

as DN)

114 days x 3 =

342 days

MRID#45640117

Because of highly 

similar structure of DN 

and DN-2-OH 

Aqueous Photolysis Half-Life 533.2 days (N/A 

- assumed same 

as DN)

533.2 days MRID#45640108

Adsorption/Desorption Coefficient (Lowest 

non-sand Kd)

N/A 2.08 Calculated for DN-2-OH 

using PCKOCwin 

program

Organic Carbon Adsorption/Desorption MRID#45640113

Coefficient (lowest non-sand KOC)

10 87

Pesticide is Wetted-In Yes Yes Proposed Label (Parent)

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other 

crops

Application Method(for max. Application 

rate)

Ground Spray(3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) (parent 0.54) 0.1304 (4) 0.0969 (5) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Water solubility was provided in the study for DN and calculated by EPI Win program for DN-2-OH.

(2). Available aerobic aquatic value was assumed for SCIGROW because the degradate formed only under aquatic condition.

(3). Maximum application rate selected for Turfgrass application.

(4). Maximum concentration observed in the aerobic soil metabolism study x application rate x mole ratio = 

 Mol wt. 173.2 EPI Win Program (0.282)(0.54)(173.2/202.2)

(5)Maximum concentration observed in the aerobic soil metabolism study x application rate x mole ratio = 

 Mol wt. 157.2 (MRID#45639707) (0.231)(0.54)(157.2/202.2)
Page 35

Table 3c Environmental Fate and Other Input Parameters for UF used in FIRST and SCIGROW

Parameter Dinotefuran UF Source

Water Solubility (25°C) 39,830 ppm 4,171 ppm MRID #45640112

EPI Win Program

Hydrolysis Half-Life (pH 7) stable stable MRID#45640102

Aerobic Soil Metabolism Half-Life (upper 

confidence bound value, 90th percentile, 

from 2 values)

116.4 days 180 days MRID#45640112

3 times single value for 

UF

MRID#45640111

Calculated (UF) using 

Biowin Program

Aerobic Soil Metabolism Half-Life (mean) 81.5 days (2) 60 days

Aerobic Aquatic Metabolism Half-life 80.8 days 360 (2 x 180 

days)

MRID#45640117

Aqueous Photolysis Half-Life 1.8 days Assumed Stable 

~500 days

MRID#45640105

Adsorption/Desorption Coefficient (Lowest 

non-sand Kd)

0.22 Not available MRID#45640114

MRID#45640113

EPI Win Program

Organic Carbon Adsorption/Desorption 

Coefficient (lowest non-sand KOC)

22 10.48

Pesticide is Wetted-In Yes Yes Proposed Label (parent)

PCA (leafy vegetable, worst case scenario) 0.87 0.87 Default value for other 

crops

Application Method(for max. Application 

rate)

Ground Spray (3) Ground Spray(3) Proposed Label

Application Rate (lb a.i./A) 0.54 0.0447 (4) Proposed Label

Applications Permitted per Year 1 1 Proposed Label

Application Interval (minimum days) N/A N/A Proposed Label

Depth of Incorporation N/A N/A Proposed Label

(1). Water solubility was provided in the study for Dinotefuran (shown for comparison purposes in this Table) and calculated

by EPI Win program for UF..

(2). Mean value was selected for SCIGROW for Dinotefuran and calculated value for UF using Biowin program.

(3). Maximum application rate selected for Turfgrass application.

(4). Maximum concentration observed in the aerobic soil metabolism study x application rate x mole ratio = 

 Mol wt. 158.2 (EPI Win) (0.106)(0.54)(158.2/202.2)
Page 36

Background Information on FIRST model:

FIRST (FQPA Index Reservoir Screening Tool) is a screening model designed to estimate the 

pesticide concentrations found in surface water for use in drinking water assessments. It 

provides high-end values on the concentrations that might be found in a small drinking water 

reservoir due to the use of pesticide. Like GENEEC, the model previously used for Tier I 

screening level, FIRST is a single-event model (one run-off event), but can account for spray 

drift from multiple applications. FIRST takes into consideration the so called Index Drinking 

Water Reservoir by representing a larger field and pond than the standard GENEEC scenario. 

The FIRST scenario includes a 427 acres field immediately adjacent to a 13 acres reservoir, 9 

feet deep, with continuous flow (two turnovers per year). The pond receives a spray drift event 

from each application plus one runoff event. The runoff event moves a maximum of 8% of the 

applied pesticide into the reservoir. This amount can be reduced due to degradation on field and 

the effect of binding to soil. Spray drift is equal to 6.4% of the applied concentration from the 

ground spray application and 16% for aerial applications.

FIRST also makes adjustments for the percent crop area. While FIRST assumes that the entire 

watershed would not be treated, the use of a PCA is still a screen because it represents the 

highest percentage of crop cover of any large watershed in the US, and it assumes that the entire 

crop is being treated. Various other conservative assumptions of FIRST include the use of a 

small drinking water reservoir surrounded by a runoff-prone watershed, the use of the maximum 

use rate, no buffer zone, and a single large rainfall.

Background Information on SCIGROW model:

SCIGROW (Screening Concentration in Ground Water) provides a groundwater screening 

exposure value to be used in determining the potential risk to human health from drinking water 

contaminated with the pesticide. Since the SCIGROW concentrations are likely to be 

approached in only a very small percentage of drinking water sources, i.e., highly vulnerable 

aquifers, it is not appropriate to use SCIGROW for national or regional exposure estimates.

SCIGROW estimates likely groundwater concentrations if the pesticide is used at the maximum 

allowable rate in areas where groundwater is exceptionally vulnerable to contamination. In most 

cases, a large majority of the use area will have groundwater that is less vulnerable to 

contamination than the areas used to derive the SCIGROW estimate.

Values below 0.006 ppb (6 ng/L) obtained by SCIGROW2.3 are beyond the scope of the 

regression data and have not been verified. If concerns are raised by exposures of less than 

0.006 ppb, a higher-tier ground water exposure assessment should be considered, regardless of 

how low a screening concentration is returned by SCIGROW. 

Background Information for EPI Win (PcKoc, and BioWin) models:
Page 37

The following overview of the PCKOCWIN and BioWin programs was obtained from the 

program manual. 

PCKOCWIN Overview

The Soil Adsorption Coefficient Program (PCKOCWIN) estimates the soil adsorption 

coeffiecient (KOC) of organic compounds. KOC can be defined as "the ratio of the amount of 

chemical adsorbed per unit weight of organic carbon (OC) in the soil or sediment to the 

concentration of the chemical in solution at equilibrium" (Lyman, 1990); it is represented by the 

following equation (Lyman, 1990):

Koc = (ug adsorbed/g organic carbon) / (ug/mL solution)

KOC provides an indication of the extent to which a chemical partitions between solid and 

solution phases in soil, or between water and sediment in aquatic ecosystems. Estimated values 

of KOC are often used in environmental fate assessment because measurement of KOC is 

expensive. Traditional estimation methods rely upon the octanol/water partition coefficient or 

related parameters, but recently the first-order molecular connectivity index (1-MCI) has been 

used successfully to predict KOC values for hydrophobic organic compounds (Sabljic, 1984, 

1987; Bahnick and Doucette, 1988). PCKOCWIN uses 1-MCI and a series of group contribution 

factors to predict Koc. The group contribution method outperforms traditional estimation 

methods based on octanol/water partition coefficients and water solubility. 

PCKOCWIN requires only a chemical structure to make these predictions. Structures are 

entered into PCKOCWIN by SMILES (Simplified Molecular Input Line Entry System) 

notations.

The first-order molecular connectivity index (MCI) has been successfully used to predict soil 

sorption coefficients (Koc) for nonpolar organics. For polar compounds, a new estimation 

method based on MCI and series of statistically derived fragment contribution factors for polar 

compounds was developed. After developing an extensive database of measured KOC values, we 

divided the dataset into a training set of 189 chemicals and an independent validation set of 205 

chemicals. Two linear regressions were then performed. First, measured log KOC values for 

nonpolar compounds in the training set were correlated with MCI. The second regression was 

developed by using the deviations between measured log KOC and the log KOC estimated with 

the nonpolar equation and the number of certain structural fragments in the polar compounds. 

The final equation for predicting log Koc accounts for 96% and 86% of the variation in the 

measured values for the training and validation sets, respectively. Results also show that the 

model outperforms and covers a wider range of chemical structures than do models based on 

octanol-water partition coefficients (KOW) or water solubility.

BIOWIN Overview

The Biodegradation Probability Program (BIOWIN) estimates the probability for the rapid 

aerobic biodegradation of an organic chemical in the presence of mixed populations of 
Page 38

environmental microorganisms. Estimates are based upon fragment constants that were 

developed using multiple linear and non-linear regression analyses.

BIOWIN requires only a chemical structure to make these predictions. Structures are entered 

into BIOWIN by SMILES (Simplified Molecular Input Line Entry System) notations. The 

BIOWIN program was developed at Syracuse Research Corporation. The prediction 

methodology was developed jointly by efforts of the Syracuse Research Corporation and the 

U.S. Environmental Protection Agency.

Two independent training sets were used to develop four mathematical models for predicting 

aerobic biodegradability from chemical structure. All four of the models are based on multiple 

regressions against counts of 36 preselected chemical substructures plus molecular weight. Two 

of the models, based on linear and nonlinear regressions, calculate the probability of rapid 

biodegradation and can be used to classify chemicals as rapidly or not rapidly biodegradable. 

The training set for these models consisted of qualitative summary evaluations of all available 

experimental data on biodegradability for 295 chemicals. The other two models allow 

semi-quantitative prediction of primary and ultimate biodegradation rates using multiple linear 

regression. The training set for these models consisted of estimates of primary and ultimate 

biodegradation rates for 200 chemicals, gathered in a survey of 17 biodegradation experts. The 

two probability models correctly classified 90% of the chemicals in their training set, whereas 

the two survey models calculated biodegradation rates for the survey chemicals with R2 = 0.7. 

These four models are intended for use in chemical screening and in setting priorities for further 

review.
Page 39

Appendix I to the Drinking Water memo

Modeling Results :

FIRST Run for Dinotefuran - Turfgrass, Ground Spray Jan 21, 2004

 RUN No. 2 FOR Dinotefuran ON Turfgrass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .540( .540) 1 1 22.039830.0 GROUND( 6.4) 87.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 138.44 0 N/A 1.80- 223.20 82.73 60.36

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 48.203 8.007

FIRST Run MNG - Turfgrass Ground spray Jan 21, 2004

 RUN No. 1 FOR MNG ON Turfgrass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .043( .043) 1 1 16.011480.0 GROUND( 6.4) 87.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 459.30 0 N/A 2.40- 297.60 918.60 224.78

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 3.860 1.631
Page 40

Modeling Results:

FIRST Run for DN (Degradate of Dinotefuran) Jan 21, 2004

 RUN No. 1 FOR DN ON Turfgrass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .097( .097) 1 1 87.0 619,400 GROUND( 6.4) 87.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 114.00 0 N/A 533.20-66116.80 342.00 340.24

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 7.774 3.322

Modeling Results:

FIRST Run for UF (Degradate of Dinotefuran) Jan 21, 2004

 RUN No. 3 FOR UF ON Turfgrass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .045( .045) 1 1 10.5 4171.0 GROUND( 6.4) 87.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 180.00 0 N/A 500.00-62000.00 360.00 357.92

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 4.069 2.070
Page 41

Modeling Results:

FIRST Run for DN-2-OH+DN-3-OH (Degradate of Dinotefuran) Jan 21, 2004

 RUN No. 1 FOR DN-2-OH ON Turfgrass * INPUT VALUES * 

 --------------------------------------------------------------------

 RATE (#/AC) No.APPS & SOIL SOLUBIL APPL TYPE %CROPPED INCORP

 ONE(MULT) INTERVAL Koc (PPM ) (%DRIFT) AREA (IN)

 --------------------------------------------------------------------

 .130( .130) 1 1 10.0 1,000,000 GROUND( 6.4) 87.0 .0

 FIELD AND RESERVOIR HALFLIFE VALUES (DAYS) 

 --------------------------------------------------------------------

 METABOLIC DAYS UNTIL HYDROLYSIS PHOTOLYSIS METABOLIC COMBINED

 (FIELD) RAIN/RUNOFF (RESERVOIR) (RES.-EFF) (RESER.) (RESER.) 

 --------------------------------------------------------------------

 60.00 0 N/A 533.20-66116.80 342.00 340.24

 UNTREATED WATER CONC (MICROGRAMS/LITER (PPB)) Ver 1.0 AUG 1, 2001

 --------------------------------------------------------------------

 PEAK DAY (ACUTE) ANNUAL AVERAGE (CHRONIC) 

 CONCENTRATION CONCENTRATION 

 --------------------------------------------------------------------

 11.881 5.952

Modeling Results :

SCIGROW Run for Dinotefuran

 

 SCIGROW

 VERSION 2.3

 ENVIRONMENTAL FATE AND EFFECTS DIVISION

 OFFICE OF PESTICIDE PROGRAMS

 U.S. ENVIRONMENTAL PROTECTION AGENCY

 SCREENING MODEL

 FOR AQUATIC PESTICIDE EXPOSURE

 

SciGrow version 2.3

chemical:Dinotefuran

time is 8/28/2003 9:12:37

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.536 1.0 0.536 2.20E+01 81.5

------------------------------------------------------------------------

groundwater screening conc. (ppb) = 2.75E+00 

************************************************************************

Modeling Results :

SCIGROW Run for MNG

 SCIGROW

 VERSION 2.3

 ENVIRONMENTAL FATE AND EFFECTS DIVISION
Page 42

 OFFICE OF PESTICIDE PROGRAMS

 U.S. ENVIRONMENTAL PROTECTION AGENCY

 SCREENING MODEL

 FOR AQUATIC PESTICIDE EXPOSURE

SciGrow version 2.3

chemical:MNG-Degradate

time is 8/28/2003 14:42:51

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.043 1.0 0.043 1.60E+01 153.1

------------------------------------------------------------------------

groundwater screening conc. (ppb) = 8.63E-01 

************************************************************************

 SCIGROW

 VERSION 2.3

SciGrow version 2.3

chemical: DN

time is 1/12/2004 10:48:26

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.096 1.0 0.096 8.70E+01 114.0

------------------------------------------------------------------------

groundwater screening conc. (ppb) = 1.88E-01 

************************************************************************

SciGrow version 2.3

chemical:UF

time is 1/13/2004 10:26:44

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.045 1.0 0.045 7.00E+00 60.0

------------------------------------------------------------------------

groundwater screening conc. (ppb) = 3.22E-01 

************************************************************************

 SCIGROW

 VERSION 2.3

 FOR AQUATIC PESTICIDE EXPOSURE

 SciGrow version 2.3

chemical: DN-2-OH

time is 1/13/2004 10:31:58

------------------------------------------------------------------------

 Application Number of Total Use Koc Soil Aerobic

 rate (lb/acre) applications (lb/acre/yr) (ml/g) metabolism (days)

------------------------------------------------------------------------

 0.130 1.0 0.130 7.00E+00 60.0

------------------------------------------------------------------------

groundwater screening conc. (ppb) = 9.38E-01 

************************************************************************
Page 43

Outputs from EPI Suite Programs for UF and DN-2-OH

SMILES : CNC(=N)NCC1(O)CCOC1

CHEM : DN-2-OH

MOL FOR: C7 H15 N3 O2 

MOL WT : 173.22

------------------------------ EPI SUMMARY (v3.10) --------------------------

Physical Property Inputs:

 Water Solubility (mg/L): ------

 Vapor Pressure (mm Hg) : ------

 Henry LC (atm-m3/mole) : ------

 Log Kow (octanol-water): ------

 Boiling Point (deg C) : ------

 Melting Point (deg C) : ------

Log Octanol-Water Partition Coef (SRC):

 Log Kow (KOWWIN v1.66 estimate) = -1.68

Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.40):

 Boiling Pt (deg C): 304.38 (Adapted Stein & Brown method)

 Melting Pt (deg C): 96.00 (Mean or Weighted MP)

 VP(mm Hg,25 deg C): 2.09E-005 (Modified Grain method)

Water Solubility Estimate from Log Kow (WSKOW v1.40):

 Water Solubility at 25 deg C (mg/L): 1e+006

 log Kow used: -1.68 (estimated)

 no-melting pt equation used

ECOSAR Class Program (ECOSAR v0.99g):

 Class(es) found:

 Aliphatic Amines

Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:

 Bond Method : 6.27E-018 atm-m3/mole

 Group Method: Incomplete

Henrys LC [VP/WSol estimate using EPI values]: 4.764E-012 atm-m3/mole

Probability of Rapid Biodegradation (BIOWIN v4.00):

 Linear Model : 0.1338

 Non-Linear Model : 0.0099

Expert Survey Biodegradation Results:

 Ultimate Survey Model: 2.5956 (weeks-months)

 Primary Survey Model : 3.4346 (days-weeks )

Readily Biodegradable Probability (MITI Model):

 Linear Model : 0.3749

 Non-Linear Model : 0.2641

Atmospheric Oxidation (25 deg C) [AopWin v1.90]:

 Hydroxyl Radicals Reaction:

 OVERALL OH Rate Constant = 186.7036 E-12 cm3/molecule-sec

 Half-Life = 0.057 Days (12-hr day; 1.5E6 OH/cm3)

 Half-Life = 0.687 Hrs

 Ozone Reaction:

 No Ozone Reaction Estimation

Soil Adsorption Coefficient (PCKOCWIN v1.66):

 Koc : 10
Page 44

 Log Koc: 1.000 

Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:

 Rate constants can NOT be estimated for this structure!

BCF Estimate from Log Kow (BCFWIN v2.14):

 Log BCF = 0.500 (BCF = 3.162)

 log Kow used: -1.68 (estimated)

Volatilization from Water:

 Henry LC: 6.27E-018 atm-m3/mole (estimated by Bond SAR Method)

 Half-Life from Model River: 1.229E+014 hours (5.121E+012 days)

 Half-Life from Model Lake : 1.341E+015 hours (5.586E+013 days)

Removal In Wastewater Treatment:

 Total removal: 1.85 percent

 Total biodegradation: 0.09 percent

 Total sludge adsorption: 1.75 percent

 Total to Air: 0.00 percent

Level III Fugacity Model:

 Mass Amount Half-Life Emissions

 (percent) (hr) (kg/hr)

 Air 1.09e-010 1.37 1000 

 Water 49.8 900 1000 

 Soil 50.1 900 1000 

 Sediment 0.0918 3.6e+003 0 

 Persistence Time: 789 hr

------------------------------------------------------------------------------

SMILES : CNC(=N)NCC1(O)CCOC1

CHEM : DN-2-OH

MOL FOR: C7 H15 N3 O2 

MOL WT : 173.22

--------------------------- BIOWIN v4.00 Results ----------------------------

 Linear Model Prediction : Does Not Biodegrade Fast

 Non-Linear Model Prediction: Does Not Biodegrade Fast

 Ultimate Biodegradation Timeframe: Weeks-Months

 Primary Biodegradation Timeframe: Days-Weeks

 MITI Linear Model Prediction : Not Readily Degradable

 MITI Non-Linear Model Prediction: Not Readily Degradable

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.1839 | -0.1839

Frag | 1 | Aliphatic ether [C-O-C] | -0.3474 | -0.3474

MolWt| * | Molecular Weight Parameter | | -0.0825

Const| * | Equation Constant | | 0.7475

============+============================================+=========+=========

 RESULT | LINEAR BIODEGRADATION PROBABILITY | | 0.1338

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 
Page 45

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -1.7232 | -1.7232

Frag | 1 | Aliphatic ether [C-O-C] | -3.4294 | -3.4294

MolWt| * | Molecular Weight Parameter | | -2.4597

============+============================================+=========+=========

 RESULT | NON-LINEAR BIODEGRADATION PROBABILITY | | 0.0099

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.2121 | -0.2121

Frag | 1 | Aliphatic ether [C-O-C] | -0.0087 | -0.0087

MolWt| * | Molecular Weight Parameter | | -0.3828

Const| * | Equation Constant | | 3.1992

============+============================================+=========+=========

 RESULT | SURVEY MODEL - ULTIMATE BIODEGRADATION | | 2.5956

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Carbon with 4 single bonds & no hydrogens | -0.1534 | -0.1534

Frag | 1 | Aliphatic ether [C-O-C] | -0.0097 | -0.0097

MolWt| * | Molecular Weight Parameter | | -0.2499

Const| * | Equation Constant | | 3.8477

============+============================================+=========+=========

 RESULT | SURVEY MODEL - PRIMARY BIODEGRADATION | | 3.4346

============+============================================+=========+=========

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

 (Primary & Ultimate) 2.00 -> months 1.00 -> longer

------------------------------------------------------------------------------

SMILES : CNC(=O)NCC1CCOC1

CHEM : UF

MOL FOR: C7 H14 N2 O2 

MOL WT : 158.20

------------------------------ EPI SUMMARY (v3.10) --------------------------

Physical Property Inputs:

 Water Solubility (mg/L): ------

 Vapor Pressure (mm Hg) : ------

 Henry LC (atm-m3/mole) : ------

 Log Kow (octanol-water): ------

 Boiling Point (deg C) : ------

 Melting Point (deg C) : ------

Log Octanol-Water Partition Coef (SRC):

 Log Kow (KOWWIN v1.66 estimate) = -0.10

Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.40):

 Boiling Pt (deg C): 291.40 (Adapted Stein & Brown method)

 Melting Pt (deg C): 79.04 (Mean or Weighted MP)

 VP(mm Hg,25 deg C): 0.000941 (Modified Grain method)

Water Solubility Estimate from Log Kow (WSKOW v1.40):

 Water Solubility at 25 deg C (mg/L): 4171
Page 46

 log Kow used: -0.10 (estimated)

 no-melting pt equation used

ECOSAR Class Program (ECOSAR v0.99g):

 Class(es) found:

 Neutral Organics

 Ureas(substituted)

Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:

 Bond Method : 2.67E-012 atm-m3/mole

 Group Method: Incomplete

Henrys LC [VP/WSol estimate using EPI values]: 4.696E-008 atm-m3/mole

Probability of Rapid Biodegradation (BIOWIN v4.00):

 Linear Model : 0.3249

 Non-Linear Model : 0.0649

Expert Survey Biodegradation Results:

 Ultimate Survey Model: 2.8409 (weeks )

 Primary Survey Model : 3.6098 (days-weeks )

Readily Biodegradable Probability (MITI Model):

 Linear Model : 0.3644

 Non-Linear Model : 0.2461

Atmospheric Oxidation (25 deg C) [AopWin v1.90]:

 Hydroxyl Radicals Reaction:

 OVERALL OH Rate Constant = 25.3856 E-12 cm3/molecule-sec

 Half-Life = 0.421 Days (12-hr day; 1.5E6 OH/cm3)

 Half-Life = 5.056 Hrs

 Ozone Reaction:

 No Ozone Reaction Estimation

Soil Adsorption Coefficient (PCKOCWIN v1.66):

 Koc : 10.48

 Log Koc: 1.020 

Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:

 Rate constants can NOT be estimated for this structure!

BCF Estimate from Log Kow (BCFWIN v2.14):

 Log BCF = 0.500 (BCF = 3.162)

 log Kow used: -0.10 (estimated)

Volatilization from Water:

 Henry LC: 2.67E-012 atm-m3/mole (estimated by Bond SAR Method)

 Half-Life from Model River: 2.758E+008 hours (1.149E+007 days)

 Half-Life from Model Lake : 3.009E+009 hours (1.254E+008 days)

Removal In Wastewater Treatment:

 Total removal: 1.85 percent

 Total biodegradation: 0.09 percent

 Total sludge adsorption: 1.76 percent

 Total to Air: 0.00 percent

Level III Fugacity Model:

 Mass Amount Half-Life Emissions

 (percent) (hr) (kg/hr)

 Air 8.65e-005 10.1 1000 
Page 47

 Water 45 360 1000 

 Soil 54.9 360 1000 

 Sediment 0.0755 1.44e+003 0 

 Persistence Time: 421 hr
48

------------------------------------------------------------------------------

SMILES : CNC(=O)NCC1CCOC1

CHEM : UF

MOL FOR: C7 H14 N2 O2 

MOL WT : 158.20

--------------------------- BIOWIN v4.00 Results ----------------------------

 Linear Model Prediction : Does Not Biodegrade Fast

 Non-Linear Model Prediction: Does Not Biodegrade Fast

 Ultimate Biodegradation Timeframe: Weeks

 Primary Biodegradation Timeframe: Days-Weeks

 MITI Linear Model Prediction : Not Readily Degradable

 MITI Non-Linear Model Prediction: Not Readily Degradable

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic ether [C-O-C] | -0.3474 | -0.3474

MolWt| * | Molecular Weight Parameter | | -0.0753

Const| * | Equation Constant | | 0.7475

============+============================================+=========+=========

 RESULT | LINEAR BIODEGRADATION PROBABILITY | | 0.3249

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic ether [C-O-C] | -3.4294 | -3.4294

MolWt| * | Molecular Weight Parameter | | -2.2465

============+============================================+=========+=========

 RESULT | NON-LINEAR BIODEGRADATION PROBABILITY | | 0.0649

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates --> Biodegrades Fast

A Probability Less Than 0.5 indicates --> Does NOT Biodegrade Fast

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic ether [C-O-C] | -0.0087 | -0.0087

MolWt| * | Molecular Weight Parameter | | -0.3496

Const| * | Equation Constant | | 3.1992

============+============================================+=========+=========

 RESULT | SURVEY MODEL - ULTIMATE BIODEGRADATION | | 2.8409

============+============================================+=========+=========

------+-----+--------------------------------------------+---------+---------

TYPE | NUM | BIOWIN FRAGMENT DESCRIPTION | COEFF | VALUE 

------+-----+--------------------------------------------+---------+---------

Frag | 1 | Aliphatic ether [C-O-C] | -0.0097 | -0.0097

MolWt| * | Molecular Weight Parameter | | -0.2282

Const| * | Equation Constant | | 3.8477

============+============================================+=========+=========

 RESULT | SURVEY MODEL - PRIMARY BIODEGRADATION | | 3.6098

============+============================================+=========+=========

Result Classification: 5.00 -> hours 4.00 -> days 3.00 -> weeks

 (Primary & Ultimate) 2.00 -> months 1.00 -> longer

------------------------------------------------------------------------------